While a good long deep hard sex sesh might strike your average bossy bottom as a basic human right, the burdens, the performance expectations, thusly placed on the willingest top might seem insuperable. We’ve all been there: his Yippie-Ki-Yay legs slung back to his shoulders, an ass simply cavernous. (But hey, he’s cute.) Definite sense of our humble seven inch being not quite enough to satisfy this one. (We’ve all been there, when they start screaming: ‘I want two cocks in me!’) Solution: big gay sex toys: dildo fun. Turn him to water first, and only at the end, sublime, stuff your cock in him.
If he likes big, you may as well start big. Dildos in the gay sex shops these days seem to range from big to massive to frankly exorbitant. Maybe start with a dildo big enough so he feels the pinch and pop as you first penetrate him. Less than that is just making washing up. (You may want to put a condom over the dildo, if it’s a casual partner. The clean-up must be scrupulous in any case.) Use a decent lube, marketed for anal sex. The high quality gay sex lubes are worth the extra penny.
Still on a cleanliness note, you might find it’s the case that anal sex with big sex toys (big comparative to average dick size) can get a little messy. You might want to think about this and set him to work with a douche in the bathroom beforehand. Get him to douche himself out, then shower down so he’s all squeaky clean. Or you might help – Some guys find it a kick.
With the dildo, start working him gently. Hold his legs back, with you at the side, and slowly pump and swivel. Assume this as the default. Bear in mind your dildo isn’t feeling it – pleasure or pain – like your penis would. Get him to make some noise, yes, but be careful about going overboard. Stop or slow if he says stop or slow, assuming you’re not playing safe words.
You can get him into a really high place with dildo sex. It might be after a while you both want to try different sex toys, which might be slower to use and dilate his anus more. Maybe try those anal toys with different textures, or inflatable butt-plugs, which can make his insides sing – but be extra careful here, with inflatable butt-plugs, for when it’s swollen big enough inside. You might want to leave a butt-plug in as you get him to suck your cock hard again, before you fuck him.
Give the most demanding bossy bottom his anal sex toy bum-fun, and he should be in just about the right place when it’s your time to get yours. Get him to suck you hard again. After all, you’ve been concentrating. His bum should be sensitized by now, so you needn’t worry about slowing down, teasing him, playing him, all that. There already. Just slam it in and get your what for.